3-Pyridinylboronic acid → 6-((3-(Methylsulfonyl)pyrrolidin-1-yl)methyl)-4-morpholino-2-(pyridin-3-yl)thieno[3,2-d]pyrimidine

HRID 390861Notes

Reaction equation

HRID 390861 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[CH3:19][S:20]([CH:23]1[CH2:27][CH2:26][NH:25][CH2:24]1)(=[O:22])=[O:21].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[CH3:19][S:20]([CH:23]1[CH2:27][CH2:26][N:25]([CH2:11][C:9]2[S:10][C:5]3[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[N:3][C:2]([C:30]4[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=4)=[N:7][C:6]=3[CH:8]=2)[CH2:24]1)(=[O:22])=[O:21]

Participants

4

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 34193563-(methylsulfonyl)pyrrolidineHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 249477946-((3-(Methylsulfonyl)pyrrolidin-1-yl)methyl)-4-morpholino-2-(pyridin-3-yl)thieno[3,2-d]pyrimidine

Procedure

2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde 10 from Example 3 (100 mg) was reacted with 3-(methanesulfonyl)pyrrolidine following the protocol in General Procedure C. One half of the crude material was then used with pyridine-3-boronic acid in General Procedure A to give 47 mg of 141 following reversed phase HPLC purification. MS (Q1) 460 (M)+.

Sources & evidence

ORD record
ord-313573adf2ea418ebf5a1eb56a719caf
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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